In 1745, a lengthy and unusual case was brought before the Venetian Executors against Blasphemy, a secular court with jurisdiction over a wide range of crimes that violated standards of morality. The parents of two young women from the Venetian mainland state were accused of pimping their two eldest daughters to Jewish men from the Venetian Ghetto in return for financial support, helping them to support their ten children. But the story became much more complicated as the court investigated the young women’s relationships; one of the daughters did seem to have a relationship with a married Jew who had promised to convert and marry her, while the other was actually a nobleman’s courtesan, supported by the same patrician who served as a guardian to a young Giacomo Casanova. Although to the patricians who served as judges, any exploitation of a young woman’s sexuality was deemed criminal, ordinary eighteenth-century Venetians saw things differently. Large families were difficult to support, and all members contributed as they were able. Typically we think of apprenticeships, domestic service, and piecework as the key strategies for supporting a family and training children for their future lives. For women, historians have long acknowledged that service carried risks of sexual exploitation, as well. But what has not been recognised as a strategy is the encouragement of premarital relations or of sex work as alternatives to domestic service and piecework. Through a microhistorical approach, this article argues that the case of the Zambelli family shows us a wider range of morally ambiguous options for supporting a large family and setting up daughters to leave the family home, many of which included threats of sexual exploitation, damaged honour, and unwanted pregnancies.